Virgin Forever - Dani

After the collapse of the Karla debacle, I went to a very dark place. It fell to my friends to try and keep me sane.

Eric and Sam joined me at the cottage for American Thanksgiving (basically just another excuse for us to have a turkey) at my cottage. It was around this time where I started to develop somewhat of an alcohol problem. Not in the sense that I was constantly bombed or drinking every night. But for a guy who usually only drinks on his birthday and on New Years Eve, going to clubs and getting bombed, and playing drinking games with friends a couple nights a week was as close to alcoholism as I'd ever come. And with a history of actual alcoholism in my family, the seed being planted in me didn't exactly thrill me.

My grades at college began to suffer as well. Don't get me wrong, I wasn't exactly a star pupil there, keeping an average between 50% and 60%, and failing a class a semester, but the depression and anxiety disorders that I already suffered from were exacerbated by the sudden removal of the best thing that had ever happened to me.

I wound up flunking out of school, and spent the summer alternating between sitting around at home feeling sorry for myself, and hanging out with some shady people.

Things began to turn around for me in the fall of 2012. September to be exact. I had gotten a job at the IT help desk of the company my dad worked for. It was only a six week contract, but I was happy for the chance to get out of the house and make some money.

As I adjusted to work there, I began to browse the personals ads on Craigslist. Unfortunately, in Toronto at least, most of the postings there by women were spam.

I took it upon myself to post my own ad, in the hopes that someone would see it amongst the spammers and assholes looking for a hookup.

I got the typical spam replies, which were promptly deleted without opening them. But I also received genuine replies from three people. Catherine, Alexandra, and Dani.

Catherine and I didn't click, and we just sort of stopped messaging each other.

Alexandra and I got along well, but she wasn't really looking for a relationship. She was pining over her ex boyfriend, and really just needed someone to talk to. They've since gotten back together, and she and I still text on a regular basis, but we've never met in person.

Dani and I got along well, and exchanged dozens of emails a day for the first couple weeks. We then moved to texting each other. I felt a good connection with her, at least as much as one can through texting.

When we finally met, it was a dream come true. It was also like pulling teeth, because Dani was very shy and needed a lot of encouragement.

We met on a Sunday at a quiet bar/lounge. We spent the evening talking, laughing, and getting to know each other, until the restaurant closed. We stood outside talking more, while I was desperately trying to work up the courage to kiss her.

I had a weak plan in mind, and I went with it.

As we were taking and laughing I would take a step forward towards her. When we were laughing at something particularly hilarious, I wrapped my arm around her waist. Before I could lose my nerve, I moved my hand to her hip, brought my free hand to her other hip, and move down to her level. I paused briefly before her, our lips inches apart to see if she would pull back, then moved in and kissed her.

Her lips were unimaginably soft and warm, with an indescribable yet delicious taste.

As we pulled away, I couldn't help but go for another quick taste, and have her another quick peck.

She smiled at me as we stood there holding each other, and told me a could've done that earlier. I'm glad I didn't, because what came next was extraordinary.

As we stood there holding each other, I was slowly running my hands up and down her back, enjoying the feeling of her body pressed into mine. We were rocking back and forth, moving incredibly slowly in a circle, like a slow dance slowed down by 90%.

As we stood there, just holding each other, we would come back together and kiss briefly, before moving back to our embrace.

Over time, I got more adventurous, and was moving my hands lower and lower with each stroke of her back. My hands eventually settled on the underside of her ass, just below the back pockets of her jeans. I started rubbing her ass, gently with little squeezes now and then. She was enjoying herself, letting out little moans and gasps, and getting more aggressive when we kissed.

Eventually I slid my hands into the back pockets of her jeans. With less fabric between my hands and her ass, I couldn't help but give her ass a good squeeze with both hands. I wasn't disappointed. She let out her loudest moan yet, and I was delighted with the feel of her ass. Soft, and forming into my hands as I gripped it, I was becoming possessed by lust for this beautiful woman.

As I would grip her ass, she would press herself into me, and soon enough we were grinding into each other on the spot. The moans and gasps, and little breaths that came from her were enough to drive me mad.

I slowly steered us towards a waist high metal patio fence that surrounded the deck area of the restaurant. We were grinding into each other that much more forcefully, as she couldn't go back at all when I came towards her.

I would grab her ass, and lift her towards me as I thrust into her. Had we been naked, this would've been the most passionate sex I had ever seen.

Like all good things, it had to end that night. It was 2AM, and I had to be up in four hours for work. Before we parted, I looked at her longingly, not wanting to leave her.

She grinned at me, said, "Come here," and pulled me into one last kiss.

She texted me the next day about how wet she had been, and I went home with the biggest case of blue balls I had ever experienced.

We got together again the following Friday, and I was determined to go farther with her.

We met at the same restaurant, again talking, laughing and generally enjoying each other. When we left, we realized it had gotten windy and had started to snow. As we walked along the storefronts, I was freezing, so we ducked into an open store.

We wandered around in there for a while, enjoying each other's company, until we decided to go to the Tim Hortons nearby.

We sat beside each other at our table, me rubbing her back with one hand, holding her hand with the other, playing with each others fingers. We stayed there for a while, enjoying each others company, never saying a word.

We eventually left and started walking back to my car, as we got close, she turned into me, pulled me into an embrace and kissed me. We started grinding almost instantly.

As it was freezing out, I got us to move into my car. We kissed, me in the driver's seat, her in the passenger, with my hand moving on her leg. As we sat there I moved my hand higher and higher.

She gave some resistance, closing her legs slightly, trying to move my hand away, but as I massaged her thigh, my fingers lightly grazing the lips of her pussy, her resistance melted away.

My focus then was entirely on rubbing her pussy over her jeans. As I did, she moaned and groaned and gasped, rocking her hips into my hand, spreading her legs wide, pulling away from me, only to come crashing back down on my hand. Her hands gripped her the door handle, my leg, her breasts, or sat idly in the air as I brought her closer and closer to ecstasy. She grabbed my hand, using it to urge my fingers harder and faster into her pussy.

As she came I continued rubbing, slowly letting her come down.

She grinned at me and we kissed.

I moved my hand to her chest, under her shirt and began to play with her breast. I had never felt a bare breast under my hand before, and I was in heaven. I squeezed her amazingly soft breast, playing with the nipple, and tried to get it out of her shirt so I could see it, to no success.

I brought her to orgasm two more times before taking her home, with a giant blister on my finger from rubbing her damp jeans for so long.

That was the last time I saw her. I kept trying to get her to come out. Eventually she gave me a BS excuse about me not seeming that into her, and said we should just be friends. I made a last ditch attempt to win her over by surprising her with flowers. She called me a stalker, and told me to leave her and her family alone.

That was the end of that, and I've yet to do anything with anyone since. Love sucks.

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